Copper-catalyzed coupling of imines, dienylstannanes, and acryloyl chlorides followed by a Diels-Alder reaction afforded hexahydro-1H-isoindolones. Diversification of the core via Pd-catalyzed cross-coupling defines a new modular approach to isoindolone combinatorial libraries.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo0621773 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Cu-Catalyzed Multicomponent Reaction of Arylhydrazines with β-Ketoesters and TBN: One-Pot Access to -Aryl 1,2,3-Triazole-1-Oxides.
J Org Chem
December 2024
Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune 411008, India.
We report a copper-catalyzed one-pot, multicomponent strategy for the convenient synthesis of -aryl 1,2,3-triazole-1-oxides using arylhydrazines, β-ketoesters, and -butyl nitrite. This mild and simple reaction proceeds in an atom-economic manner with broad substrate scope, affording a variety of -aryl 1,2,3-triazole-1-oxide derivatives. Other salient features of the reaction are good functional group tolerance, scalability, and product diversification.
View Article and Find Full Text PDFPhotocatalysis Meets Copper Catalysis: A New Opportunity for Asymmetric Multicomponent Radical Cross-Coupling Reactions.
Acc Chem Res
December 2024
Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
Article Synopsis
- Radical-mediated cross-coupling reactions are a powerful method for creating diverse molecular structures, but they face challenges in controlling reaction pathways and selectivity due to the high reactivity of radicals.
- The use of visible-light photoredox catalysis combined with chiral copper catalysts can enhance control over radical species and improve enantioselective reactions.
- This research focuses on innovative strategies for chiral C-C and C-O bond formation by utilizing dual photoredox/copper catalysis, highlighting the effectiveness of visible light in achieving selectivity in these reactions.
A Sonochemical and Mechanochemical One-Pot Multicomponent/Click Coupling Strategy for the Sustainable Synthesis of Bis-Heterocyclic Drug Scaffolds.
Chempluschem
January 2025
Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, Guanajuato, C.P. 36050, Gto., México.
Bis-heterocycles were synthesized via a consecutive one-pot process by a Groebke-Blackburn-Bienaymé reaction (GBB-3CR) followed by Copper-catalyzed Alkyne-Azide Cycloaddition (CuAAC) assisted by alternative sustainable energies (ASE) such as ultrasonic and mechanical. These efficient and convergent strategies allowed the in situ generation of complex azides functionalized with imidazo[1,2-a]pyridines (IMPs), which was used as a synthetic platform. The target molecules contain two privileged scaffolds in medicinal chemistry: IMPs and the heterocyclic bioisostere of trans-amide bond, the 1,4-disubstituted 1H-1,2,3-triazoles (1,4-DS-1,2,3-Ts).
View Article and Find Full Text PDFAsymmetric Conjugate Addition of Vinyl Arene-Derived Chiral Benzylcopper Nucleophiles.
Org Lett
October 2024
Department of Chemistry, Sungkyunkwan University, Suwon 16419, Korea.
We report the copper-catalyzed asymmetric conjugate addition of vinyl arene-derived nucleophiles to α,β-unsaturated diesters. Due to the high electrophilicity of α,β-unsaturated diesters toward nucleophilic copper catalysts, inclusion of vinyl arenes as pronucleophiles is challenging due to chemoselectivity issues in a multicomponent reaction compared with those of other successful examples of dienes, allenes, and enynes. In this method, chemoselective generation of a chiral benzylic copper intermediate and its stereoselective addition to α,β-unsaturated diesters provided organoboron adducts with contiguous stereogenic centers with good levels of diastereoselectivity and enantioselectivity (≤85:15 diastereomeric ratio and 99% enantiomeric excess, respectively).
View Article and Find Full Text PDFAdvancing drug discovery: Thiadiazole derivatives as multifaceted agents in medicinal chemistry and pharmacology.
Bioorg Med Chem
October 2024
Department of Microbiology, University of Ilorin, Ilorin, Nigeria.
In this dispensation of rapid scientific and technological advancements, significant efforts are being made to curb health-related diseases. Research discoveries have highlighted the value of heterocyclic compounds, particularly thiadiazole derivatives, due to their diverse pharmacological activities. These compounds play a crucial role in therapeutic medicine and the development of effective drugs.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!